I know that chronology is something that shouldn't be attempted to work out in regards to comics, particularly Batman, and that what qualifies for this query is very subjective, however;
What comics cover major pivotal moments regarding major supporting heroic allies of Batman, (not including other stand alone heroes like Superman)?
Obviously I will be liberally with spoilers in this thread, so won't use any spoiler tags, lest I put the entire post in one... You have been warned!
That being said, as far as I've been able to ascertain;
Dick Grayson joins Batman as Robin - Detective Comics #38 (retold many times, for example in Long Halloween and All-Star Batman and Robin)
Barbera Gorden becomes Batgirl - Detective Comics #359
Dick Grayson becomes Nightwing - I can't ascertain where this originally happened, but retold in Nightwing - Year 1
Jason Todd becomes the second Robin - Detective Comics #526
Damian Wayne is born - Son of the Demon
Jason Todd dies - Batman #426–429 (Collected in a Death in the Family)
Barbera Gorden is maimed - The Killing Joke
Barbera Gorden becomes Oracle - Suicide Squad #23
Tim Drake becomes Robin - Batman #442 (Collected in a Lonely Place of Dying)
Jason Todd lives - Batman #638 (Collected in Under the Hood)
Tim Drake resigns - ?
Stephanie Brown becomes Robin - Robin #126
Damien Wayne is revealed - Batman #655 (Collected in Batman & Son)
Stephanie Brown dies (but she's not really dead, of course) - War Crimes
Damian Wayne becomes Robin - Batman and Robin #1
So, I'm taking it that is roughly right? I've obviously left out characters like Batwoman, as a relic of the 60's campness, and earlier incarnations of Batgirl who were the niece, or some such?!?!
Anyway, the reason I started thinking about all this, and my main question is, were there a sequence of comics where Dick became increasingly disillusioned with him up to his leaving Batman? What issues did this actually happen in? Are they worth reading?! I understand he was Nightwing long before he actually left Batman anyway?!?! Does Nightwing - Year 1 sort of cover all of this anyway?!
I'm asking mainly because I've read Long Halloween, Son of the Demon, Killing Joke, Death in the Family, Lonely Place of Dying and Under the Hood (and, actually, I like them in that order, in that I don't really like LPoD or UtH at all), and I'm interested if any of the other pivotal moments involving these characters are worth reading at all?! It seems that as time has gone on, these events get more and more frequent, and have less and less impact?! And if anyone dies, that it's almost certain that they aren't actually dead, and will be back at some point?! I think reading Under the Hood actually retroactively made Death in the Family worse for me... :(